1729 CHEROKEE DRIVE Sarasota, FL $ 4,450,000
1729 CHEROKEE DRIVE
$ 4,450,000
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1729 CHEROKEE DRIVE

Sarasota, FL, 34239
$ 4,450,000
Bedrooms4 Baths4.1 Sq 4,353

Monthly Estimate*

$ 27,399

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Single Family Home for sale in Sarasota, FL

for $4,450,000 with 4 bedrooms and 4 full baths, 1 half bath. This 4,353 square foot home was built in 2008 on a lot size of 0.46.

Recipient of eleven awards, including Residential Design and Build Design Excellence and Home of the Year by SRQ Magazine, this exceptional residence is the result of a thoughtful collaboration between Jonathan Parks Architect and Michael A. Gilkey Inc landscape designer. Located in one of Sarasota’s oldest and most established neighborhoods, the home seamlessly blends a traditional 1920s architectural vocabulary with a modern appreciation for simplicity and precision. The result is a sophisticated four-bedroom residence with a British Colonial sensibility—elegant, timeless, and thoughtfully designed for today’s lifestyle. Set on an unusually large 20,000-square-foot lot and located outside of any flood zone, the property offers a rare sense of space and privacy. An artistic pool and a series of designated outdoor living areas, framed by curated garden vignettes, complete this tranquil retreat. The striking foyer welcomes you with understated elegance, gleaming wood floors, and an immediate sense of refinement. Walls of glass define the main living spaces, filling the interior with natural light and highlighting the fireplace as a focal point. While the classic elements of a traditional home remain—stucco exterior, white roof, and ironwork details—the overall aesthetic is contemporary and quietly confident. Large windows and an open floor plan are designed to maximize light and create a seamless connection to the outdoors. A spacious screened patio offers an inviting setting for both relaxation and al fresco dining. Mature Mahoe trees, native to South Africa, line the exterior and rise gracefully to the level of the home’s high windows, enhancing privacy and serenity. The primary suite occupies its own private wing on the first floor, complete with a secluded courtyard, while an ensuite guest bedroom and office balance the opposite wing. Upstairs, two additional ensuite bedrooms each enjoy private balconies overlooking the lush grounds. Throughout the home, a Zen-like sense of peace and tranquility prevails—a true sanctuary of thoughtful design and quiet luxury.

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Single Family Active

Price

$ 4,450,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 24,980

Style

Custom

Lot Size

0.46

Year Built

2008

Town/City

Sarasota

County/Region

Sarasota

MLS | Web ID

A4682051

Features
General
Sewer Public Sewer
Heating Central Electric Zoned
Cooling Central Air Mini-Split Unit(s)
Utilities Cable Connected Electricity Connected Natural Gas Connected Phone Available Sprinkler Well Street Lights Water Connected
Roof Concrete Tile
Appliances Built-In Oven Cooktop Dishwasher Disposal Dryer Gas Water Heater Microwave Range Range Hood Refrigerator Washer Water Purifier Water Softener
Zoning RSF1
Garage Spaces 3
Patio/Porch Features Covered Patio Porch Screened
Architectural Style Custom
Pool Features Heated In Ground Lighting Tile
Security Features Security System Smoke Detector(s)
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 2008
View Trees/Woods
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Sarasota
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name CHEROKEE PARK 2
Facing Direction South
Garage Y/N true
Total Rooms 11
Full Baths 4
Status Active
Directions From S Osprey Ave turn onto Cherokee Dr and house will be on the right side.
High School Sarasota High
City SARASOTA
Senior Community Y/N false
MLS Area 34239 - Sarasota/Pinecraft
Lot Size Units Square Feet
Lot Size Square Feet 20000
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated In Ground
Elementary School Southside Elementary
Land Lease Y/N false
Tax Annual Amount 24980.69
Middle/Junior High School Booker Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://pix360.com/phototour3/41648/
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 4
Legal Description W 1/2 OF LOT 4 BLK F CHEROKEE PARK
Pet Size Limit Extra Large (101+ Lbs.)
Minimum Lease 1 Month
Water Access Y/N false
Additional Rooms Den/Library/Office Great Room Inside Utility
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) High Ceilings Kitchen/Family Room Combo Primary Bedroom Main Floor Solid Surface Counters Solid Wood Cabinets Split Bedroom Stone Counters Thermostat Vaulted Ceiling(s) Walk-In Closet(s) Window Treatments
Flooring Ceramic Tile Engineered Hardwood Other
Furnished Y/N Unfurnished
Fireplace Features Gas Living Room Outside Wood Burning
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Window Treatments
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities Balcony Courtyard French Doors Irrigation System Lighting Outdoor Grill Outdoor Kitchen Private Entrance Private Yard Rain Gutters
Vegetation Mature Landscaping Trees/Landscaped
Fencing Fenced
Parking Features Driveway Garage Door Opener Oversized
Lot Features City Lot Landscaped Near Public Transit Oversized Lot Private Sidewalk
Water Source Public
Lot Size Area 20000
Foundation Details Slab
Spa true
Building Area Total 5995
Lot Size Acres 0.46
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 3
Road Frontage Type Street Paved
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Michael Saunders & Company

Broker

kimogilvie@michaelsaunders.com

Email

Affordability Calculator

$29,481
Per Month
93%
7%
0%
Monthly Principal & Interest
$27,399
Monthly Property Taxes
$2,082
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Sarasota High High School High School
Pricing History
DatePricePrice ChangeDescription
2/12/2026$4,450,000 Listed Price

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1729 CHEROKEE DRIVE, Sarasota, FL, 34239 is a Single Family Home for sale at $4,450,000 with 4,353 sqft and a lot size of 0.46. 1729 CHEROKEE DRIVE has 4 bedrooms, 4.1 baths, and was built in 2008. The property's zip code is 34239 which is in Sarasota, FL